Ethyl chloroformate → 2-(1-(3-Phenoxyphenyl)-2-oxabicyclo[2.2.2]octan-4-yl)acetyl azide
Reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([C:14]23[CH2:21][CH2:20][C:17]([CH2:22][C:23]([OH:25])=O)([CH2:18][CH2:19]2)[CH2:16][O:15]3)[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC(OCC)=O.[N-:32]=[N+:33]=[N-:34].[Na+]>CC(C)=O.O>[O:1]([C:8]1[CH:9]=[C:10]([C:14]23[CH2:21][CH2:20][C:17]([CH2:22][C:23]([N:32]=[N+:33]=[N-:34])=[O:25])([CH2:18][CH2:19]2)[CH2:16][O:15]3)[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 2-(1-(3-phenoxyphenyl)-2-oxabicyclo[2.2.2]octan-4-yl)acetic acid (6A: 97 mg, 0.287 mmol) in acetone (1 mL) at 0° C. was added TEA (0.064 mL, 0.459 mmol), followed by ethyl chloroformate (0.044 mL, 0.459 mmol) dropwise. The mixture was stirred at 0° C. for 30 min. A solution of NaN3 (37.3 mg, 0.573 mmol) in 0.5 mL water was added slowly and the mixture was stirred at 0° C. for another 1 h. The reaction mixture was then poured into ice-water (5 mL) and extracted with diethyl ether (3×2 mL). The combined extracts were washed successively with water (5 mL), saturated aqueous NaHCO3 (5 mL) and water (5 mL), dried over Na2SO4, filtered, and concentrated in vacuo to afford the title compound (104 mg, 100% yield). LCMS, [M+Na]+=386.1.
Workup
- stirringthe mixture was stirred at 0° C. for another 1 h
- extractionextracted with diethyl ether (3×2 mL)
- washThe combined extracts were washed successively with water (5 mL), saturated aqueous NaHCO3 (5 mL) and water (5 mL)
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-8bfb622a7777453d941f2a3cb54b4c1c
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08962660B2
Reaction notes
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